Pyranine
{{chembox
| Watchedfields = changed
| verifiedrevid = 426193536
| ImageFile = Pyranine.svg
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| ImageAlt = Skeletal formula of pyranine
| IUPACName = Trisodium 8-hydroxypyrene-1,3,6-trisulfonate
| OtherNames = 8-Hydroxypyrene-1,3,6-trisulfonic acid; Solvent Green 7; HPTS; Sulfonated hydroxy pyrene trisodium salt
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6358-69-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = I2W85YOX9L
| EINECS = 228-783-6
| PubChem = 4136521
| StdInChI=1S/C16H10O10S3.3Na/c17-11-5-12(27(18,19)20)8-3-4-10-14(29(24,25)26)6-13(28(21,22)23)9-2-1-7(11)15(8)16(9)10;;;/h1-6,17H,(H,18,19,20)(H,21,22,23)(H,24,25,26);;;/q;3*+1/p-3
| StdInChIKey = KXXXUIKPSVVSAW-UHFFFAOYSA-K
| SMILES = C1=CC2=C3C(=C(C=C2S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC4=C(C=C(C1=C43)O)S(=O)(=O)[O-].[Na+].[Na+].[Na+]
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|Section2={{Chembox Properties
| C=16 | H=7 | Na=3 | O=10 | S=3
| Appearance = Yellow-green crystalline powder
| Density =
| MeltingPt =
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| Solubility = Soluble
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|Section3={{Chembox Hazards
| FlashPt =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|}}
| AutoignitionPt =
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Pyranine is a hydrophilic, pH-sensitive fluorescent dye from the group of chemicals known as arylsulfonates.{{cite web| url = http://www.chemindustry.com/chemicals/1196265.html| title = chem industry entry| access-date = 2007-12-31| archive-date = 2007-10-26| archive-url = https://web.archive.org/web/20071026155704/http://www.chemindustry.com/chemicals/1196265.html| url-status = dead}}{{cite web | url= http://ctdbase.org/detail.go?type=chem&acc=C005047 | title = Comparative Toxicogenomics Database entry}} Pyranine is soluble in water and is used as a coloring agent, biological stain, optical detecting reagent, and pH indicator.{{cite web|url=http://chemicalland21.com/lifescience/foco/PYRANINE.htm|title=chemical land 21 entry}}{{cite web | url = http://sci-toys.com/scichem/jqp000/4136521.html | title= Sci-Toys entry}} Pyranine is also used in yellow highlighters to provide their characteristic fluorescence and bright yellow-green colour. It is also found in some types of soap.{{cite web |url=https://www.whatsinproducts.com/chemicals/view/1/115 |title=D&C Green No. 8 (C.I. 59040) |website=whatsinproducts.com |accessdate=2023-05-04}}
Synthesis
Pyranine is synthesized from pyrenetetrasulfonic acid and a solution of sodium hydroxide in water under reflux.{{cite journal|last1=Tietze|first1=Ernst|last2=Bayer|first2=Otto|title=Die Sulfosäuren des Pyrens und ihre Abkömmlinge|journal=Justus Liebig's Annalen der Chemie|volume=540|issue=1|year=1939|pages=189–210|issn=0075-4617|doi=10.1002/jlac.19395400113}} The trisodium salt crystallizes as yellow needles when adding an aqueous solution of sodium chloride.
See also
References
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External links
- [http://ctdbase.org/detail.go?type=chem&acc=C005047 CTD's Pyranine page] from the Comparative Toxicogenomics Database